Acetic Acid → N-[(1S,2R)-1-benzyl-2-hydroxy-3-(1-propyl-butylamino)-propyl]-3-(2-oxo-pyrrolidin-1-yl)-5-pentyloxy-benzamide

HRID 852673ノート

反応式

HRID 852673 の反応式
[NH2:1][CH2:2][C@@H:3]([OH:33])[C@@H:4]([NH:12][C:13](=[O:32])[C:14]1[CH:19]=[C:18]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH:17]=[C:16]([N:26]2[CH2:30][CH2:29][CH2:28][C:27]2=[O:31])[CH:15]=1)[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH3:48][CH2:49][CH2:50][C:51](=O)[CH2:52][CH2:53][CH3:54].CC(O)=O>C(Cl)Cl>[CH2:5]([C@H:4]([NH:12][C:13](=[O:32])[C:14]1[CH:19]=[C:18]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH:17]=[C:16]([N:26]2[CH2:30][CH2:29][CH2:28][C:27]2=[O:31])[CH:15]=1)[C@H:3]([OH:33])[CH2:2][NH:1][CH:51]([CH2:52][CH2:53][CH3:54])[CH2:50][CH2:49][CH3:48])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

参加物

6

反応物 4

HCID 176Acetic AcidHCID 312464-HeptanoneHCID 5049666Sodium triacetoxyborohydrideHCID 69357401N-((1S,2R)-3-amino-1-benzyl-2-hydroxy-propyl)-3-(2-oxo-pyrrolidin-1-yl)-5-pentyloxy-benzamide

生成物 1

HCID 69356145N-[(1S,2R)-1-benzyl-2-hydroxy-3-(1-propyl-butylamino)-propyl]-3-(2-oxo-pyrrolidin-1-yl)-5-pentyloxy-benzamide収率 11.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of N-((1S,2R)-3-amino-1-benzyl-2-hydroxy-propyl)-3-(2-oxo-pyrrolidin-1-yl)-5-pentyloxy-benzamide (E182) (30 mg, 0.066 mmol, 1 equiv) in (CH2Cl)2 (5 ml) were added sodium triacetoxyborohydride (20 mg, 0.094 mmol, 1.4 equiv), 4-heptanone (10 μl, 0.070 mmol, 1.1 equiv) and CH3COOH (4 μl, 0.070 mmol, 1,1 equiv). The resulting mixture was stirred at room temperature for 92 hours, diluted with CH2Cl2, washed with saturated aqueous NaHCO3 solution, dried over MgSO4 and concentrated in vacuo. Purification of the residue by flash chromatography on silica gel (iso-hexane/ethyl acetate: 3/2) gave N-[(1S,2R)-1-benzyl-2-hydroxy-3-(1-propyl-butylamino)-propyl]-3-(2-oxo-pyrrolidin-1-yl)-5-pentyloxy-benzamide (4.2 mg, 11%) as a colourless oil. [M+H]+=552.2, RT=2.98 min

後処理

  1. washwashed with saturated aqueous NaHCO3 solution
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customPurification of the residue by flash chromatography on silica gel (iso-hexane/ethyl acetate: 3/2)

出典と根拠

ORDレコード
ord-0bc3adc8599742329258e927c37c1bd9
出典データセット
uspto-grants-2007_08
特許番号
US07253198B2

反応ノート

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